WO1997002238A1 - Hydrazones d'acide fluorobutenique - Google Patents

Hydrazones d'acide fluorobutenique Download PDF

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Publication number
WO1997002238A1
WO1997002238A1 PCT/EP1996/002743 EP9602743W WO9702238A1 WO 1997002238 A1 WO1997002238 A1 WO 1997002238A1 EP 9602743 W EP9602743 W EP 9602743W WO 9702238 A1 WO9702238 A1 WO 9702238A1
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Prior art keywords
spp
formula
compounds
alkyl
fluorine
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PCT/EP1996/002743
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German (de)
English (en)
Inventor
Udo Kraatz
Wolfram Andersch
Andreas Turberg
Norbert Mencke
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Bayer Aktiengesellschaft
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Priority to AU64151/96A priority Critical patent/AU6415196A/en
Publication of WO1997002238A1 publication Critical patent/WO1997002238A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/28—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/72—Hydrazones
    • C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom

Definitions

  • the present invention relates to new fluorobutenic acid hydrazones, processes for their preparation and their use for controlling animal
  • Pests in particular insects, arachnids and nematodes, which occur in agriculture, in the forests, in the protection of stocks and materials, and in the hygiene sector.
  • R 1 represents hydrogen or halogen
  • R 2 and R 3 independently of one another represent hydrogen, alkyl or in each case optionally substituted aryl or hetaryl,
  • R and R together with the carbon atom to which they are attached form an optionally substituted carbocyclic or heterocyclic ring.
  • the compounds of the formula (I) can be in the form of geometric and / or optical isomers or isomer mixtures of different compositions.
  • the invention relates to both the pure isomers and the isomer mixtures. It has further been found that the fluorobutenic acid hydrazones of the formula (I) are obtained when
  • R 2 R 3 C N-NH 2 (II)
  • R 2 and R 3 have the meaning given above
  • R 1 has the meaning given above
  • R 1 has the meaning given above
  • (I) have pronounced biological properties and are particularly suitable for controlling animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in the forests, in the protection of stored products and materials and in the hygiene sector.
  • the fluorobutenic acid hydrazones according to the invention are generally defined by the formula (I).
  • R 1 preferably represents hydrogen, fluorine, chlorine or bromine.
  • R 2 and R 3 independently of one another preferably represent hydrogen, C j -C ⁇ -
  • Alkyl optionally by fluorine, chlorine, bromine, nitro, cyano, amino, C j - C 6 alkyl, C r C 6 haloalkyl, C r C 6 alkoxy, C r C 6 haloalkoxy, C r C 6 - alkylthio, C 1 -C 6 haloalkylthio, C j -C 8 alkylamino or di-C j -C 8 - alkylamino-substituted phenyl or is optionally substituted by fluorine, chlorine, bromine or C j -C 4 alkyl-substituted hetaryl having 5 or 6
  • R 2 and R 3 together with the carbon atom to which they are attached form a 4- to 9-membered ring which is optionally oxygen, sulfur or nitrogen (which is optionally substituted by C 1 -C 8 -alkyl, phenyl or benzyl ) contains.
  • R 1 particularly preferably represents hydrogen or fluorine.
  • R 2 and R 3 independently of one another particularly preferably represent hydrogen
  • C 1 -C 6 alkyl optionally by fluorine, chlorine, nitro, amino, CC 4 -
  • R 2 and R 3 together with the carbon atom to which they are attached form a 5- or 6-membered carbocycle.
  • hydrocarbon radicals such as alkyl or alkenyl
  • alkyl or alkenyl are straight-chain or branched as far as possible, even in conjunction with heteroatoms such as alkoxy or alkylthio.
  • CF 2 CF-CH 2 - CONH-No-L OHC --c ⁇
  • Process A) described above for the preparation of compounds of the formula (I) is characterized in that hydrazones of the formula (II) are reacted with acid chlorides of the formula (III), if appropriate in the presence of a diluent and if appropriate in the presence of a base .
  • Process A) according to the invention is preferably carried out in the presence of a diluent.
  • Suitable diluents are, in particular, organic solvents, for example chlorinated aliphatic or aromatic hydrocarbons such as cyclohexane, toluene, xylene, dichloromethane, dichloroethane, chloroform or chlorobenzene, ethers such as diethyl ether, dioxane or tetrahydrofuran, nitriles such as acetonitrile or sulfoxides such as dimethyl sulfoxide.
  • organic solvents for example chlorinated aliphatic or aromatic hydrocarbons such as cyclohexane, toluene, xylene, dichloromethane, dichloroethane, chloroform or chlorobenzene, ethers such as diethyl ether, dioxane or tetrahydrofuran, nitriles such as acetonitrile or sulfoxides such as dimethyl sulfoxide.
  • Two-phase systems consisting of water and an organic solvent, for example water / methylene chloride or water / toluene, are also suitable as diluents.
  • organic solvent for example water / methylene chloride or water / toluene
  • all organic or inorganic bases suitable for such acylation reactions can be used as the base
  • Amines are preferably used, especially tertiary amines such as triethylamine, diazabicycloundecene (DBU), diazabicyclonones (DBN), diazabicycloctane (DABCO) or pyridine or alkali metal or alkaline earth metal carbonates, hydrogen carbonates or hydroxides.
  • tertiary amines such as triethylamine, diazabicycloundecene (DBU), diazabicyclonones (DBN), diazabicycloctane (DABCO) or pyridine or alkali metal or alkaline earth metal carbonates, hydrogen carbonates or hydroxides.
  • DBU diazabicycloundecene
  • DBN diazabicyclonones
  • DABCO diazabicycloctane
  • pyridine alkali metal or alkaline earth metal carbonates, hydrogen carbonates or hydroxides. Examples include sodium carbonate, potassium carbonate, Sodium
  • the reaction temperature in process A) can be varied within a substantial range. In general, temperatures between -10 ° C and 180 ° C, preferably between 0 ° C and 100 ° C.
  • the molar ratio of the compound of formula (II) to the compound of formula (III) is generally 3 1 to 1 3, preferably 1.5 1 to 1 1.5
  • the reaction is generally carried out under normal pressure
  • reaction mixture is hydrolyzed and that
  • Process B) described above for the preparation of compounds of the formula (I) is characterized in that acylhydrazines of the formula (IV) are reacted with carbonyl compounds of the formula (V), if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst
  • Halogenated aliphatic or aromatic hydrocarbons such as cyclohexane, toluene, xylene, dichloromethane are preferably usable,
  • the reaction can also be carried out without a solvent. In this case, it may be advantageous to use the carbonyl compound of the formula (V) in excess.
  • Suitable catalysts are sulfonic acids such as p-toluenesulfonic acid.
  • reaction temperatures can be varied within a wide range in process B) described above. In general, temperatures between 0 ° C and 160 ° C, preferably between 20 ° C and 130 ° C.
  • the reaction is generally carried out at normal pressure.
  • the reaction mixture is worked up in a conventional manner, for example by distilling off the diluent.
  • Formula (II) are known and / or can be prepared in a simple manner by known methods.
  • hydrazones of the formula (II) are obtained, for example, if carbonyl compounds of the formula (V) are reacted with hydrazine.
  • acylhydrazines of the formula (IV) required as starting materials in the preparation process B) can be prepared in a simple manner by reacting acid chlorides of the formula (III) with hydrazine or with tert-butyloxycarbonylhydrazine and subsequent acidic cleavage.
  • the carbonyl compounds of the formula (V) are generally known compounds of organic chemistry.
  • the active substances are suitable for controlling animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species and against all or individual stages of development.
  • the pests mentioned above include:
  • Thysanura e.g. Lepisma saccharina.
  • Orthoptera e.g. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp.
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.
  • From the order of the Heteroptera for example Eury gaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
  • From the order of the Homoptera for example Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigususpp.
  • Cacoecia podana Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Drosophila melanogaster Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tabanus spp.
  • Tannia spp. Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.
  • Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp.
  • Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp ..
  • the compounds of the formula (I) according to the invention are distinguished in particular by an excellent nematicidal action, for example against Meloidogyne incognita. They have a systemic effect and can be used on the leaf.
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as very fine encapsulation in polymeric substances.
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents
  • Agents ie emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • a liquid solvent Aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols are essentially suitable , such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Aromatics such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlor
  • Possible solid carriers are, for example, ammonium salts and natural rock powders, such as kaolins, clays,
  • Talc such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours and
  • Granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks, as emulsifiers and / or foam-generating agents are possible, for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are, for example, lignin sulfite waste liquor and methyl cellulose
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations
  • additives can be mineral and vegetable oils
  • Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used
  • the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%
  • the active substance according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active substances, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • the insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms and others
  • Fungicides 2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2 ', 6'-dibromo-2-methyl-4 , -trifluoromethoxy-4 , -trifluoromethyl-1, 3-thiazole-5-carboxanilide; 2,6-dichloroN- (4-trifluoromethylbenzyl) benzamide; (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) acetamide; 8-hydroxyquinoline sulfate; Methyl- (E) -2- ⁇ 2- [6- (2-cyano-phenoxy) pyrimidin-4-yloxy] phenyl ⁇ -3-methoxyacrylate; Methyl (E) methoximino [alpha- (o-tolyloxy) -o-tolyl] acetate; 2-phenylphenol (OPP), aldimorph, ampropylfos
  • Dichlorophene diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodine, drazoxolone.
  • Edifenphos epoxyconazole, ethirimol, etridiazole,
  • Bacillus thuringiensis Bendiocarb, Benfuracarb, Bensultap, Betacyfluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxin,
  • Fenamiphos fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb,
  • Fenoxycarb Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb,
  • Imidacloprid Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin, Lambda-cyhalothrin, Lufenuron, Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos,
  • Methamidophos methidathione, methiocarb, methomyl, metolcarb, milbemectin,
  • Promecarb Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophos,
  • Tebufenozid Tebufenpyrad
  • Tebupirimphos Teflubenzuron
  • Tefluthrin Temephos
  • the active compounds according to the invention can furthermore be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
  • Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms
  • the active ingredient When used against hygiene pests and pests of stored products, the active ingredient is distinguished by an excellent residual action on wood and clay as well as a good stability to alkali on limed substrates.
  • the active compounds according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, Featherlings and fleas.
  • animal parasites ectoparasites
  • tick ticks leather ticks
  • mites running mites
  • flies stinging and licking
  • parasitic fly larvae lice, hair lice, Featherlings and fleas.
  • Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota ., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp.,
  • Morellia spp. Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp ., Melophagus spp ..
  • Siphonaptrida for example Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp ..
  • the Heteropterida for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp ..
  • Mesostigmata e.g. Argas spp., Ornithodorus spp., Otabius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillneu- spp., Pill monyssus spp., Sternostoma spp., Varroa spp ..
  • Actinedida Prostigmata
  • Acaridida e.g. Acarapis spp., Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodterol spp ., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp ..
  • the active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are used in agricultural animals, such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalos, rabbits, chickens, turkeys, ducks,
  • Geese bees, other pets such as Dogs, cats, house birds, aquarium fish and so-called experimental animals such as Infest hamsters, guinea pigs, rats and mice.
  • Infest hamsters guinea pigs, rats and mice.
  • the active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, such as Example by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implant tate, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing, powdering and with the help of active ingredient-containing shaped bodies such as collars , Ear tags, tail tags, limb bands, holsters, marking devices, etc.
  • enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories
  • parenteral administration such as Example
  • the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or apply after 100 to 10,000-fold dilution or use it as a chemical bath.
  • formulations for example powders, emulsions, flowable agents
  • log p decimal logarithm of the n-octanol / water distribution coefficient, determined by HPLC analysis on reversed phase with
  • CF 2 CF-CH 2 -CO-NH-NH 2 x CF 3 COOH
  • Test nematode Meloidogyne incognita solvent. 4 parts by weight of acetone
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • the active ingredient preparation is intimately mixed with soil that is heavily contaminated with the test nematodes.
  • the treated soil is poured into pots and lettuce and the pots are kept at a greenhouse temperature of 25 ° C
  • the lettuce roots are examined for nematode infestation (root galls) and the degree of effectiveness of the active ingredient is determined in%.
  • the degree of effectiveness is 100% if the infestation is avoided completely, it is 0% if the infestation is exactly as high as that of the Control plants in untreated but contaminated soil in the same way
  • Test animals Adult suckled females
  • the test is carried out in 5-fold determination. 1 ⁇ l of the solutions is injected into the abdomen, the animals are transferred to dishes and stored in an air-conditioned room. The effect is determined by the inhibition of egg laying. 100% means that no tick has laid.
  • the compounds according to Preparation Examples 2, 5 and 7 showed an activity of 100% at an exemplary active ingredient concentration of 20 ⁇ g / animal.
  • Test animals Lucilia cuprina larvae (OP-resistant)
  • 30 to 50 larvae per concentration are placed on horse meat (1 cm) in glass tubes, onto which 500 ⁇ l of the dilution to be tested are pipetted.
  • the glass tubes are placed in plastic beakers, the bottom of which is covered with sea sand, and stored in an air-conditioned room (26 ° C ⁇ 1.5 ° C, 70% relative humidity ⁇ 10%). The effects are checked after 24 hours and 48 hours (larvicidal action). After the larvae have emigrated (approx. 72 h), the glass tubes are removed and perforated plastic lids are placed on the beakers. After l' ⁇ times the development period (hatching of the control flies), the hatched flies and the dolls / doll covers are counted.
  • Larvae after 48 h (larvicidal effect), or the inhibition of adult hatching from the pupa or the inhibition of pupa formation.
  • the criterion for the in vitro effect of a substance is the inhibition of flea development or a development standstill before the adult stage. 100% larvicidal activity means that all larvae have died after 48 hours. 100% development inhibitory effect means that no adult flies have hatched.
  • Example D the compound according to Preparation Example 7 showed an activity of 100% at an exemplary active ingredient concentration of 1000 ppm.
  • the effectiveness of the active substance preparation is determined. The effectiveness is expressed in%. 100% means that all the flies have been killed, 0% means that none of the flies have been killed
  • the compound according to Preparation Example 7 showed an effectiveness of 100% at an exemplary active ingredient concentration of 1000 ppm.

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  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne de nouvelles hydrazones d'acide fluorobuténique de la formule (I), dans laquelle R1 désigne hydrogène ou halogène, R2 et R3 désignent indépendamment l'un de l'autre hydrogène, alkyle ou aryle éventuellement substitué ou hétaryle éventuellement substitué, ou forment, conjointement avec l'atome de carbone auquel il sont liés, un composé carbocyclique ou hétérocyclique éventuellement substitué. L'invention concerne en outre des procédés permettant de les préparer et des les utiliser pour lutter contre des animaux parasites.
PCT/EP1996/002743 1995-07-05 1996-06-24 Hydrazones d'acide fluorobutenique WO1997002238A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU64151/96A AU6415196A (en) 1995-07-05 1996-06-24 Fluorobutenoic acid hydrazones

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19524435.4 1995-07-05
DE1995124435 DE19524435A1 (de) 1995-07-05 1995-07-05 Fluorbutensäurehydrazone

Publications (1)

Publication Number Publication Date
WO1997002238A1 true WO1997002238A1 (fr) 1997-01-23

Family

ID=7766045

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1996/002743 WO1997002238A1 (fr) 1995-07-05 1996-06-24 Hydrazones d'acide fluorobutenique

Country Status (3)

Country Link
AU (1) AU6415196A (fr)
DE (1) DE19524435A1 (fr)
WO (1) WO1997002238A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8895556B2 (en) 2007-12-26 2014-11-25 Critical Outcome Technologies Inc. Compounds and method for treatment of cancer
US8987272B2 (en) 2010-04-01 2015-03-24 Critical Outcome Technologies Inc. Compounds and method for treatment of HIV
US9284275B2 (en) 2007-01-11 2016-03-15 Critical Outcome Technologies Inc. Inhibitor compounds and cancer treatment methods

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4950666A (en) * 1989-03-30 1990-08-21 Fmc Corporation Difluoroalkane and difluoroalkenylalkane pesticides
WO1992015555A2 (fr) * 1991-03-01 1992-09-17 Monsanto Company Composes fluoroalcenyles et utilisation de ces composes comme insecticides

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4950666A (en) * 1989-03-30 1990-08-21 Fmc Corporation Difluoroalkane and difluoroalkenylalkane pesticides
WO1992015555A2 (fr) * 1991-03-01 1992-09-17 Monsanto Company Composes fluoroalcenyles et utilisation de ces composes comme insecticides

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9284275B2 (en) 2007-01-11 2016-03-15 Critical Outcome Technologies Inc. Inhibitor compounds and cancer treatment methods
US8895556B2 (en) 2007-12-26 2014-11-25 Critical Outcome Technologies Inc. Compounds and method for treatment of cancer
US8987272B2 (en) 2010-04-01 2015-03-24 Critical Outcome Technologies Inc. Compounds and method for treatment of HIV
US9422282B2 (en) 2010-04-01 2016-08-23 Critical Outcome Technologies Inc. Compounds and method for treatment of HIV
US9624220B2 (en) 2010-04-01 2017-04-18 Critical Outcome Technologies Inc. Compounds and method for treatment of HIV

Also Published As

Publication number Publication date
DE19524435A1 (de) 1997-01-09
AU6415196A (en) 1997-02-05

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